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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:29:05 UTC

Update Date

2022-03-07 02:55:15 UTC

HMDB ID

HMDB0037244

Secondary Accession Numbers

HMDB37244

Metabolite Identification

Common Name

(8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide

Description

(8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide has been detected, but not quantified in, fats and oils. This could make (8alpha,10beta,11beta)-3-hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0037244
     RDKit          3D
(8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide
 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.8431   -2.4591   -0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2867   -1.3278    0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1101   -1.3736    0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.1025    0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -0.7771    1.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283   -0.1855    1.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4232   -0.1085    1.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1017    0.3699   -0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6211    1.7947   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6824    0.3118   -0.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    0.4894   -1.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6027    0.6605   -1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5817   -0.0277   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654    0.4177   -0.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5553    0.7062    0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8919    1.6862    1.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634   -3.2748    0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4826   -2.0722   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271   -2.8844   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -1.3798    1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0389   -0.3937    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2117   -1.3321   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1851   -1.8352    0.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6249   -0.2443   -0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1771    2.2551    0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808    2.3329   -0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7310    1.7827    0.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2562    0.9890    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2416    1.4341   -1.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024   -0.2819   -2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0331    1.5319   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0803    1.3024   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -0.3822   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6262    1.0151    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6018   -0.2064    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2397    2.5690    1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13  2  1  0
 10  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  END


  Mrv0541 05061309392D          

 16 17  0  0  0  0            999 V2000
    4.6713   -1.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680    1.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7524   -0.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5774   -0.9200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130   -0.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  2  0  0  0  0
 10  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14  6  1  0  0  0  0
 15 13  2  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037244

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CC=C(CCO)C(C)CC2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O3/c1-8-7-12-11(9(2)13(15)16-12)4-3-10(8)5-6-14/h3,8-9,11-12,14H,4-7H2,1-2H3

> <INCHI_KEY>
MOXJTUNOIGNZKZ-UHFFFAOYSA-N

> <FORMULA>
C13H20O3

> <MOLECULAR_WEIGHT>
224.2961

> <EXACT_MASS>
224.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.396497841625937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(2-hydroxyethyl)-3,7-dimethyl-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-2-one

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
1.5983680169999994

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.989018410645652

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9288002973080407

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
62.173700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(2-hydroxyethyl)-3,7-dimethyl-3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037244
     RDKit          3D
(8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide
 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.8431   -2.4591   -0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2867   -1.3278    0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1101   -1.3736    0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.1025    0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -0.7771    1.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283   -0.1855    1.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4232   -0.1085    1.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1017    0.3699   -0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6211    1.7947   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6824    0.3118   -0.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    0.4894   -1.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6027    0.6605   -1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5817   -0.0277   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654    0.4177   -0.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5553    0.7062    0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8919    1.6862    1.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634   -3.2748    0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4826   -2.0722   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271   -2.8844   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -1.3798    1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0389   -0.3937    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2117   -1.3321   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1851   -1.8352    0.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6249   -0.2443   -0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1771    2.2551    0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808    2.3329   -0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7310    1.7827    0.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2562    0.9890    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2416    1.4341   -1.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024   -0.2819   -2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0331    1.5319   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0803    1.3024   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -0.3822   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6262    1.0151    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6018   -0.2064    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2397    2.5690    1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13  2  1  0
 10  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.720  -2.975   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.114   2.327   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.968  -0.384   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.738  -1.717   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.278  -1.717   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.144  -0.384   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.590  -1.629   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    4   10                                                       
CONECT    4    3   11                                                       
CONECT    5    6   10                                                       
CONECT    6    5   14                                                       
CONECT    7    8   12                                                       
CONECT    8    1    7   10                                                  
CONECT    9    2   11   13                                                  
CONECT   10    3    5    8                                                  
CONECT   11    4    9   12                                                  
CONECT   12    7   11   16                                                  
CONECT   13    9   15   16                                                  
CONECT   14    6                                                            
CONECT   15   13                                                            
CONECT   16   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0037244
HETATM    1  C1  UNL     1      -1.843  -2.459  -0.585  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.287  -1.328   0.295  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.110  -1.374   0.574  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.487  -1.102   0.589  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.148  -0.777   1.787  1.00  0.00           O  
HETATM    6  C5  UNL     1       3.328  -0.186   1.338  1.00  0.00           C  
HETATM    7  O2  UNL     1       4.423  -0.109   1.969  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.102   0.370  -0.062  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.621   1.795  -0.005  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.682   0.312  -0.080  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.850   0.489  -1.269  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.603   0.660  -1.113  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.582  -0.028  -0.490  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.965   0.418  -0.525  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.555   0.706   0.836  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.892   1.686   1.530  1.00  0.00           O  
HETATM   17  H1  UNL     1      -2.263  -3.275   0.003  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.483  -2.072  -1.388  1.00  0.00           H  
HETATM   19  H3  UNL     1      -0.927  -2.884  -1.093  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.957  -1.380   1.186  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.039  -0.394   1.155  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.212  -1.332  -0.571  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.185  -1.835   0.105  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.625  -0.244  -0.795  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.177   2.255   0.921  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.281   2.333  -0.919  1.00  0.00           H  
HETATM   27  H11 UNL     1       4.731   1.783   0.086  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.256   0.989   0.724  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.242   1.434  -1.759  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.102  -0.282  -2.061  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.033   1.532  -1.599  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.080   1.302  -1.181  1.00  0.00           H  
HETATM   33  H17 UNL     1      -3.585  -0.382  -0.975  1.00  0.00           H  
HETATM   34  H18 UNL     1      -4.626   1.015   0.682  1.00  0.00           H  
HETATM   35  H19 UNL     1      -3.602  -0.206   1.452  1.00  0.00           H  
HETATM   36  H20 UNL     1      -3.240   2.569   1.237  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   13   20
CONECT    3    4   21   22
CONECT    4    5   10   23
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   10   24
CONECT    9   25   26   27
CONECT   10   11   28
CONECT   11   12   29   30
CONECT   12   13   13   31
CONECT   13   14
CONECT   14   15   32   33
CONECT   15   16   34   35
CONECT   16   36
END

HMDB0037244
     RDKit          3D
(8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide
 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.8431   -2.4591   -0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2867   -1.3278    0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1101   -1.3736    0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4871   -1.1025    0.5887 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -0.7771    1.7871 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283   -0.1855    1.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4232   -0.1085    1.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1017    0.3699   -0.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6211    1.7947   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6824    0.3118   -0.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    0.4894   -1.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6027    0.6605   -1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5817   -0.0277   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9654    0.4177   -0.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5553    0.7062    0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8919    1.6862    1.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634   -3.2748    0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4826   -2.0722   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271   -2.8844   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571   -1.3798    1.1862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0389   -0.3937    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2117   -1.3321   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1851   -1.8352    0.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6249   -0.2443   -0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1771    2.2551    0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2808    2.3329   -0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7310    1.7827    0.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2562    0.9890    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2416    1.4341   -1.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024   -0.2819   -2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0331    1.5319   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0803    1.3024   -1.1809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -0.3822   -0.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6262    1.0151    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6018   -0.2064    1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2397    2.5690    1.2373 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 13  2  1  0
 10  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(8a,10b,11b)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide	Generator
(8Α,10β,11β)-3-hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide	Generator

Chemical Formula

C₁₃H₂₀O₃

Average Molecular Weight

224.2961

Monoisotopic Molecular Weight

224.141244506

IUPAC Name

6-(2-hydroxyethyl)-3,7-dimethyl-2H,3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-2-one

Traditional Name

6-(2-hydroxyethyl)-3,7-dimethyl-3H,3aH,4H,7H,8H,8aH-cyclohepta[b]furan-2-one

CAS Registry Number

342372-61-6

SMILES

CC1C2CC=C(CCO)C(C)CC2OC1=O

InChI Identifier

InChI=1S/C13H20O3/c1-8-7-12-11(9(2)13(15)16-12)4-3-10(8)5-6-14/h3,8-9,11-12,14H,4-7H2,1-2H3

InChI Key

MOXJTUNOIGNZKZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037244)

Source

Endogenous

Endogenous (HMDB: HMDB0037244)

Exogenous

Food

Food (HMDB: HMDB0037244)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0037244)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0037244)

Role

Biological role

Energy source (HMDB: HMDB0037244)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037244)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.88 g/L	ALOGPS
logP	2.21	ALOGPS
logP	1.6	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	16.99	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.17 m³·mol⁻¹	ChemAxon
Polarizability	25.4 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	151.254	31661259
DarkChem	[M-H]-	150.527	31661259
DeepCCS	[M+H]+	146.593	30932474
DeepCCS	[M-H]-	142.805	30932474
DeepCCS	[M-2H]-	180.371	30932474
DeepCCS	[M+Na]+	155.909	30932474
AllCCS	[M+H]+	153.2	32859911
AllCCS	[M+H-H2O]+	149.3	32859911
AllCCS	[M+NH4]+	156.8	32859911
AllCCS	[M+Na]+	157.9	32859911
AllCCS	[M-H]-	157.8	32859911
AllCCS	[M+Na-2H]-	158.3	32859911
AllCCS	[M+HCOO]-	158.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	5.11 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9007 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.07 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2022.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	299.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	452.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	515.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	921.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	388.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1227.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	306.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	340.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	321.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	283.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	90.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide	CC1C2CC=C(CCO)C(C)CC2OC1=O	2971.2	Standard polar	33892256
(8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide	CC1C2CC=C(CCO)C(C)CC2OC1=O	1908.5	Standard non polar	33892256
(8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide	CC1C2CC=C(CCO)C(C)CC2OC1=O	1975.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide,1TMS,isomer #1	CC1CC2OC(=O)C(C)C2CC=C1CCO[Si](C)(C)C	1936.7	Semi standard non polar	33892256
(8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide,1TBDMS,isomer #1	CC1CC2OC(=O)C(C)C2CC=C1CCO[Si](C)(C)C(C)(C)C	2170.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01t9-3900000000-fb06058b67e632b15024	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide GC-MS (1 TMS) - 70eV, Positive	splash10-00ei-4590000000-d8064e3688fedcfda922	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide 10V, Positive-QTOF	splash10-056r-0490000000-1bdc3036fb99d8834166	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide 20V, Positive-QTOF	splash10-0a7i-0940000000-e8ab234f262557eff3b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide 40V, Positive-QTOF	splash10-0540-8900000000-18ea318a98a39cf4d801	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide 10V, Negative-QTOF	splash10-00di-0690000000-ea6e1f7dff2e2dcf731c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide 20V, Negative-QTOF	splash10-05i3-0950000000-e3253556336b750dd7cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide 40V, Negative-QTOF	splash10-0f9f-5900000000-54d6632731b76b567e0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide 10V, Positive-QTOF	splash10-0a6r-0390000000-9eab637f18bf80316a4e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide 20V, Positive-QTOF	splash10-00fr-0910000000-07e8368f349c958cad89	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide 40V, Positive-QTOF	splash10-00lj-9700000000-730c2781dba588274e8f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide 10V, Negative-QTOF	splash10-00di-0090000000-25ff68a3fa868b5c35d3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide 20V, Negative-QTOF	splash10-0fmi-1940000000-1778e56a176f2fd21449	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide 40V, Negative-QTOF	splash10-0kkm-2900000000-ec012141bdba4e50996f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016255

KNApSAcK ID

Not Available

Chemspider ID

35014394

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73232471

PDB ID

Not Available

ChEBI ID

138761

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide (HMDB0037244)

MOL for HMDB0037244 ((8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide)

3D MOL for HMDB0037244 ((8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide)

3D SDF for HMDB0037244 ((8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide)

3D-SDF for HMDB0037244 ((8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide)

PDB for HMDB0037244 ((8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide)

3D PDB for HMDB0037244 ((8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide)

SMILES for HMDB0037244 ((8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide)

INCHI for HMDB0037244 ((8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide)

Structure for HMDB0037244 ((8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide)

3D Structure for HMDB0037244 ((8alpha,10beta,11beta)-3-Hydroxy-4,15-dinor-1(5)-xanthen-12,8-olide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra